While it may be a stretch to describe the average player character as an upstanding citizen, most campaigns do assume that they are not actively at odds with the law. Turning this assumption on its head can lead to a memorable campaign.
The first thing to consider when creating an outlaw campaign is why the characters are outlaws. Some characters may be wrongly accused. Others may be outlaws because of a crisis of conscience. Of course, some characters may simply be outlaws because they actually are criminals.
One advantage running a campaign where the characters are wrongly accused is that it can happen to anyone. It doesn’t matter whether the character is the most noble paladin or the most shady rogue, both have to deal with the consequences of being accused of a crime that they didn’t commit.
The wrongly accused hero is a common trope in fiction, from characters like Jean Valjean in Les Misérables to James Bond in License to Kill. Because of the serial nature of a campaign, it might be best to explore TV shows like The Fugitive, The A-Team, and even The Incredible Hulk for inspiration.
In all of these cases, the protagonists are constantly looking for a way to clear their names. However, the story often involves them being drawn into helping other people with their problems. This is to keep the plots from becoming to repetitive.
These shows also involved the protagonists staying one step ahead of their pursuers. Having the characters being actively pursued, especially by a reoccurring antagonist, makes sure the campaign doesn’t lose its flavor.
It is probably a good idea for the characters to get an opportunity to clear their names before the campaign comes to a close. If the campaign ends without this opportunity, it will probably leave the players feeling unfulfilled. On the other hand, if the characters finally clear their names after numerous sessions of life on the run, the campaign will probably be one that the players talk about long after it is over.
Crisis of Conscience
Probably the most famous example of the crisis of conscience outlaw is Robin Hood. In most modern versions of the myth, Robin Hood becomes an outlaw because cannot abide the suffering being inflicted on the poor, but he cannot work within the corrupt system to stop it.
This campaign premise requires at least one character to be moral enough to make the initial decision to break the law to uphold its spirit. Not every character needs to stand on that high moral ground, but most should be working to achieve the same goals. After all, it doesn’t make sense that a single moral man (or woman) would be working with an entirely immoral group.
One advantage that a crisis of conscience campaign has over the wrongly accused campaign is that the characters have a good reason to stick around and fight. While characters in the wrongly accused campaign will often be looking to flee their pursuers, characters in a crisis of conscience campaign would never have become outlaws in the first place if they didn’t have a reason to stick around and fight.
A crisis of conscience campaign should eventually allow the characters the chance to right the injustice they became outlaws to fight. Like the wrongly accused campaign above, the players will probably be left feeling unfulfilled unless they get their chance to make things right. On the plus side, overthrowing a corrupt government makes for a truly epic way to end the campaign.
The easiest way for the characters to end up on the wrong side of the law is to run a criminal based campaign. A campaign based around a thieves guild or piracy would be an easy way to assure that the characters are on the wrong side of the law.
Of course, this requires the characters be the type that would be law-breakers in the first place. I would suggest shying away from completely evil and depraved characters. While such characters may be fun in a one-shot game, in a campaign they are often problematic. Looking to antiheroes like Jack Sparrow or to the multi-layered mobsters of The Sopranos is a good source of inspiration for characters in this kind of campaign.
One difficulty in DMing a criminal campaign is that criminals are traditionally more proactive than heroes in literature. While a hero may come across a heist and disrupt it, a criminal is the one who actually plans the heist to begin with.
Placing your protagonists in a criminal organization will help with this issue. Regardless, it is probably a good idea to prep several mini-adventures suited to the criminal mindset. That way, if the characters decide they wish to rob a merchant or blackmail a noble, you can have something prepped and ready.
Oh, and talking with your players in advance to figure out what they want to do with their characters is probably a good idea too. If the players are willing to work with you, they can drive the plot while you deliver the twists!